Solange Knowles

Performing at the Northside Festival in Brooklyn last month, Knowles opted for a casual on top (Babatunde Bafing Fitted Cap ($20) and striped tee), party on the bottom (below-the-knee gladiator heels) approach to her denim shorts.

Cara Delevinge

Spotted in Paris, the British model gave her denim shorts the ‘90s hip-hop treatment with the addition of a beanie, Burberry Prorsum leather jacket, Worn By Squeeze This! T-Shirt ($56), and Nike Air Jordan sneakers.